Effect of the U‑Shaped Cavity of Conformationally Flexible Chiral Lewis-Acidic Boron-Based Catalysts in Multiselective Diels–Alder Reactions

The effect of the U-shaped cavity of conformationally flexible chiral Lewis acidic boron-based catalysts in multiselective Diels–Alder reactions was investigated. The U-shaped catalysts can recognize substituents at the terminal acetylene moiety of propynal based on steric factors and can also recog...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (17), p.3607-3611
Main Authors: Sakamoto, Tatsuhiro, Toh, Kohei, Matsui, Kai, Hatano, Manabu, Ishihara, Kazuaki
Format: Article
Language:English
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Summary:The effect of the U-shaped cavity of conformationally flexible chiral Lewis acidic boron-based catalysts in multiselective Diels–Alder reactions was investigated. The U-shaped catalysts can recognize substituents at the terminal acetylene moiety of propynal based on steric factors and can also recognize alkyne and alkene substrates based on the match/mismatch between the catalysts and substrates. Moreover, even in a mixture of different catalysts and substrates, the desired competitive reactions can proceed multiselectively. This proof-of-concept study should contribute to the development of artificial enzyme-like catalysis in vitro.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01060